Nitrosative cytosine deamination. An exploration of the chemistry emanating from deamination with pyrimidine ring-opening

Chemical Research in Toxicology

Volumn 18, Issue 8, 2005, Pages 1211-1218

  Rayat, Sundeep ^a   Qian, Ming ^a   Glaser, Rainer ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOCARBONYLPHENYLCARBAMATE; 2 CYANO 1 TERT BUTYLVINYLCARBAMATE; 3 AMINOACRYLONITRILE; 3 ISOCYANATOACRYLONITRILE; CARBAMIC ACID DERIVATIVE; CYTOSINE; CYTOSINEDIAZONIUM ION; ETHYL 2 CYANOVINYLCARBAMATE; ION; NITRILE; PYRIMIDINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; DEAMINATION; DECARBOXYLATION; DIAZOTIZATION; ELECTRICITY; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; NITROSATION; OLIGOMERIZATION; POLYMERIZATION; REACTION ANALYSIS; RING OPENING; STRUCTURE ANALYSIS;

CARBAMATES; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIZATION; CYTOSINE; DEAMINATION; HYDROLYSIS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NITROGEN; PYRIMIDINES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 23844498152     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050082a     Document Type: Article

References (73)

1. (a) Schärer, O. D. (2003) Chemistry and biology of DNA repair. Angew. Chem., Int. Ed. 42, 2946-2974.
2. (b) Ronen, A., and Glickman, B. W. (2001) Human DNA repair gene. Environ. Mol. Mutagen. 37, 241-283.
3. Kossel, A., and Steudel, H. (1903) Weitere Untersuchungen über das cytosin. Z. Physiol. Chem. 38, 49-59.
4. Kossel, A., and Steudel, H. (1903) Ueber das vorkommen des uracils im thierkörper. Z. Physiol. Chem. 37, 245-247.
5. (a) Wyszynski, M., Gabbara, S., and Bhagwat, A. S. (1994) Cytosine deaminations catalyzed by DNA cytosine methyltransferases are unlikely to be the major cause of mutational hot spots at sites of cytosine methylation in Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 91, 1574-1578.
6. (b) Yebra, M. J., and Bhagwat, A. S. (1995) A cytosine methyltransferase converts 5-methylcytosine in DNA to thymine. Biochemistry 34, 14752-14757.
7. (c) Sharath, A. N., Weinhold, E., and Bhagwat, A. S. (2000) Reviving a dead enzyme: cytosine deaminations promoted by an inactive DNA methyltransferase and an S-adenosylmethionine analogue. Biochemistry 39, 14611-14616.
8. Pham, P., Bransteitter, R., and Goodman, M. F. (2005) Reward versus risk: DNA cytidine deaminases triggering immunity and disease. Biochemistry 44, 2703-2715.
9. Shaffer, P. M., Hsu, C.-A., and Abbott, M. T. (1975) Metabolism of pyrimidine deoxyribonucleosides in Neurospora crassa. J. Bacteriol. 121, 648-655.
10. Lieb, M., and Bhagwat, A. S. (1996) Very short patch repair: reducing the cost of cytosine methylation. Mol. Microbiol. 20, 467-473.
11. (a) Lindahl, T. (1974) N-glycosidase from Escherichia coli that releases free uracil from DNA containing deaminated cytosine residues. Proc. Natl. Acad. Sci. U.S.A. 71, 3649-3653.
12. (b) Tye, B. K., Chien, J., Lehman, I. R., Duncan, B. K., and Warner, H. R. (1978) Uracil incorporation: a source of pulse-labeled DNA fragments in the replication of the Escherichia coli chromosome. Proc. Natl. Acad. Sci. U.S.A. 75, 233-237.
13. (c) Wallace, S. S. (1988) AP endonucleases and DNA glycosylases that recognize oxidative DNA damage. Environ. Mol. Mutagen. 12, 431-477.
14. (a) Sagher, D., and Strauss, B. (1983) Insertion of nucleotides opposite apurinic apyrimidinic sites in deoxyribonucleic acid during in vitro synthesis: uniqueness of adenine nucleotides. Biochemistry 22, 4518-4526.
15. (b) Loeb, L. A., and Cheng, K. C. (1990) Errors in DNA synthesis: a source of spontaneous mutations. Mutat. Res. 238, 297-304.
16. Pattinson, J. K., Millar, D. S., McVey, J. H., Grundy, C. B., Wieland, K., Mibashan, R. S., Martinowitz, U., Tan-Un, K., Vidaud, M., Goossens, M., Sampietro, M., Mannucci, P. M., Krawczek, M., Reiss, J., Whitmore, B., Zoll, D., Bowcock, S., Wensley, R., Ajani, A., Mitchell, V., Rizza, C., Maia, R., Winter, P., Mayne, E. E., Schwartz, M., Green, P. J., Kakkar, V. V., Tuddenham, E. G. D., and Cooper, D. N. (1990) The molecular genetic analysis of hemophilia A: a directed search strategy for the detection of point mutations in the human factor VIII gene. Blood 76, 2242-2248.
17. Goate, A., Chartier-Harlin, M. C., Mullan, M., Brown, J., Crawford, F., Fidani, L., Giuffra, L., Haynes, A., and Irving, N. (1991) Segregation of a missense mutation in the amyloid precursor protein gene with familial Alzheimer's disease. Nature 349, 704-706.
18. Hollstein, M., Sidransky, D., Vogelstein, B., and Harris, C. C. (1991) p53 Mutations in human cancers. Science 253, 49-53.
19. Yandell, D. W., Campbell, T. A., Dayton, S. H., Petersen, R., Walton, D., Little, J. B., McConkie-Rosell, A., Buckley, E. G., and Dryja, T. P. (1989) Oncogenic point mutations in the human retinoblastoma gene: their application to genetic counseling. N. Engl. J. Med. 321, 1689-1695.
20. Hsiao, K., Baker, H. F., Crow, T. J., Poulter, M., Owen, F., Terwilliger, J. D., Westaway, D., Ott, J., and Prusiner, S. B. (1989) Linkage of a prion protein missense variant to Gerstmann-Straussler syndrome. Nature 338, 342-345.
21. Caulfield, J. L., Wishnok, J. S., and Tannenbaum, S. R. (1998) Nitric oxide-induced deamination of cytosine and guanine in deoxynucleosides and oligonucleotides. J. Biol. Chem. 273, 12689-12695.
22. Frederico, L. A., Kunkel, T. A., and Shaw, B. R. (1990) A sensitive genetic assay for the detection of cytosine deamination: determination of rate constants and the activation energy. Biochemistry 29, 2532-2537.
23. Wink, D. A., Kasprzak, K. S., Maragos, C. M., Elespuru, R. K., Misra, M., Dunams, T. M., Cebula, T. A., Koch, W. H., Andrews, A. W., Allen, J. S., and Keefer, L. K. (1991) DNA deaminating ability and genotoxicity on nitric oxide and its progenitors. Science 254, 1001-1003.
24. Glaser, R., Rayat, S., Lewis, M., Son, M.-S., and Meyer, S. (1999) Theoretical studies of DNA base deamination. 2. Ab initio study of DNA base diazonium ions and of their linear, unimolecular dediazoniation paths. J. Am. Chem. Soc. 121, 6108-6119.
25. Rayat, S., and Glaser, R. (2003) 5-Cyanoimino-4-oxomethylene-4,5- dihydroimidazole and nitrosative guanine deamination. A theoretical study of geometries, electronic structures, and N-protonation. J. Org. Chem. 68, 9882-9892.
26. Rayat, R., Wu, Z., and Glaser, R. (2004) Nitrosative guanine deamination: Ab initio study of deglycation of N-protonated 5-cyanoimino-4-oxomethylene-4,5- dihydroimidazoles. Chem. Res. Toxicol. 17, 1157-1169.
27. 18O-labeling experiments. J. Am. Chem. Soc. 126, 9960-9969.
28. Qian, M., and Glaser, R. (2004) 5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: experimental evidence for pyrimidine ring-opening during deamination. J. Am. Chem. Soc. 126, 2274-2275.
29. Qian, M., and Glaser, R. (2005) Demonstration of an alternative mechanism for G-to-G cross-link formation. J. Am. Chem. Soc. 127, 880-887.
30. Glaser, R., and Rayat, S. (2005) Intermediates formed by unimolecular dediazoniation of cytosinediazonium ion: phenyl cation analogs, azaryne cations, cyclic nitrilium ions, or even acyclic cations? J. Am. Chem. Soc., submitted.
31. Hodgen, B., Rayat, S., and Glaser, R. (2003) Nitrosative adenine deamination: facile pyrimidine ring-opening in the dediazoniation of adeninediazonium ion. Org. Lett. 5, 4077-4080.
32. Wilson, D. M., III, and Barsky, D. (2001) The major human abasic endonuclease: formation, consequences and repair of abasic lesions in DNA. Mutat. Res. 485, 283-307.
33. Glaser, R., Wu, H., and Saint Paul, F. v. (2005) Chemical carcinogens in non-enzymatic cytosine deamination: 3-isocyanatoacrylonitrile. J. Mol. Model., submitted.
34. Badawi, H. M., Förner, W., and Al-Saadi, A. (2001) C-C and C-N rotational barriers in vinyl ketene and vinyl isocyanate. THEOCHEM 535, 183-197.
35. (a) Nakashima, K., Takeshita, T., and Morimoto, K. (2002) Review of the occupational exposure to isocyanates: mechanisms of action. Environ. Health Prev. Med. 7, 1-6.
36. (b) Karol, M. H., and Jin, R. (1991) Mechanisms of immunotoxicity to isocyanates. Chem. Res. Toxicol. 4, 503-509.
37. (a) Trembley, P., Lesagem J., Ostiguy, C., and Van Tra, H. (2003) Investigation of the competitive rate of derivatization of several secondary amines with phenylisocyanate (PHI), hexamethylene-1,6-diisocyanate (HDI), 4,4′-methylenebis(phenyl isocyanate) (MDI) and toluene diisocyanate (TDI) in liquid medium. Analyst 128, 142-149.
38. (b) Schwetlick, K., Noack, R., and Stebner, F. (1994) Three fundamental mechanisms of base-catalyzed reactions of isocyanates with hydrogen-acidic compounds. J. Chem. Soc., Perkin Trans. 2, 599-608.
39. Tiger, R. P., Levina, M. A., Entelis, S. G., and Andreev, M. A. (2002) Molecular organization of reagents in the kinetics and catalysis of liquid-phase reactions. XI. Manifestation of the structure of solution in the kinetics of water addition to isocyanate in water-dioxane mixtures. Kinet. Catal. 43, 662-666.
40. Raspoet, G., Nguyen, M. T., McGarraghy, M., and Hegarty, A. F. (1998) Experimental and theoretical evidence for a concerted catalysis by water clusters in the hydrolysis of isocyanates. J. Org. Chem. 63, 6867-6877.
41. (a) Satchell, D. P. N., and Satchell, R. S. (1975) Acylation by ketenes and isocyanates. Mechanistic comparison. Chem. Soc. Rev. 4, 231-250.
42. (b) Saunders, J. H., and Frisch, K. C. (1962) Polyurethanes, Chemistry and Technology, Interscience, New York.
43. Yamamoto, T., Hirasawa, S., and Muraoka, M. (1985) Synthesis of β-(alkylimino) α-cyano dithiocarboxylic acids, 3-alkyl-1,3-thiazine- 2,6-dithiones, and related compounds. Bull. Chem. Soc. Jpn. 58, 771-772.
44. (a) Alberola, A., Antolin, L. F., Gonzalez, A. M., Laguna, M. A., and Pulido, F. J. (1986) Base-induced ring cleavage of 4-functionalized 3-unsubstituted isoxazoles. Synthesis of 5-amino azoles and 4-cyano azoles. J. Heterocyclic Chem. 23, 1035-1038.
45. (b) Cocco, M. T.; Congiu, C.; Onnis, V. (1995) Propenethioamides in the synthesis of heterocyclic systems. Synthesis of pyrrole and 1,4-thiazepine derivatives. J. Heterocycl. Chem. 32, 1679-1682.
46. Wu, H., and Glaser, R. (2005) Amino-effect on the protonation of beta-aminoacrylonitrile. Chem. Res. Toxicol. 18, 111-114.
47. Ishikawa, F., Yamaguchi, H., Saegusa, J., Inamura, K., Mimura, T., Nishi, T., Sakuma, K., and Ashida, S. (1985) Cyclic guanidines. XVI. Synthesis and biological activities of tetracyclic imidazo[2,1-b]quinazolinone derivatives. Chem. Phar. Bull. 33, 3336-3348.
48. Hegarty, A. F., Frost, L. N., and Coy, J. H. (1974) Question of amide group participation in carbamate hydrolysis. J. Org. Chem. 39, 1089-1093.
49. Pretch, E., Clerc, T., Simon, W., and Seibl, J. (1989) Tables of Spectral Data For Structure Determination of Organic Compounds, 2nd ed., Springer-Verlag, New York.
50. Schmidt, H. (1987) Synthese neuer 4-hydroxybenzonitrilderivate und deren herbizide eigenschaften. Monatsh. Chemie 118, 217-228.
51. Ishikawa, F., Yamaguchi, H., Saegusa, J., Inamura, K., Mimura, T., Nishi, T., Sakuma, K., and Ashida, S. (1985) Cyclic guanidines. XVI. Synthesis and biological activities of tetracyclic imidazo[2,1-b]quinazolinone derivatives. Chem. Phar. Bull. 33, 3336-3348.
52. (a) Herbig, K., Huisgen, R., and Huber, H. (1966) cis-trans-Isomerization of enamine β-carboxylic acid esters. Steric course of the amine addition to carboxylic acid esters of the acetylene series. Chem. Ber. 99, 2526-2545.
53. (b) Herbig, K., Huisgen, R., and Huber, H. (1966) cis-trans-Isomerization of enamine β-carboxylic acid esters. Steric course of the amine addition to carboxylic acid esters of the acetylene series. Chem. Ber. 99, 2546-2555.
54. Boldt, P., Militzer, H., Thielecke, W., and Schulz, L. (1968) Direct tert-alkylation of CH-acidic compounds. Liebigs Ann. Chem. 718, 101-104.
55. Neumann, N., and Boldt, P. (1984) Hydrogenation of substituted 1,1-cyclopropane-dicarbonitriles. Chem. Ber. 117, 1935-1939.
56. Angeles, E., Santillan, A., Martinez, I., Ramirez, A., Moreno, E., Salmon, M., and Martinez, R. (1994) A simple method for the synthesis of carbamates. Synth. Commun. 24, 2441-2447.
57. 4. Angew. Chem., Int. Ed. Engl. 8, 457-458.
58. Peeters, H., Prange, U., and Vogt, W. (1982) Method of preparing beta-alkoxyacrylonitrile. U.S. Patent 4,319,024.
59. Jaafar, I., Francis, G., Danion-Bougot, R., and Danion, D. (1994) α-Isocyanatoacrylonitriles from alkylidene- or arylidenecyanoacetic acids; synthesis and reactions. Synthesis 56-60.
60. Cacchi, S., Misiti, D., and Torre, F. L. (1980) Amides from nitriles using basic hydrogen peroxide under phase-transfer catalyzed conditions. Synthesis 243-244.
61. Bendale, P. M., and Khadilkar, B. M. (2000) Selective hydrolysis of nitriles to amides using NaOH-PEG under microwave irradiation. Synth. Commun. 30, 1713-1718.
62. Merchant, K. J. (2000) Potassium trimethylsilanolate mediated hydrolysis of nitriles to primary amides. Tetrahedron Lett. 4, 3747-3749.
63. Hall, J. H., and Gisler, M. (19760) A simple method for converting nitriles to amides. Hydrolysis with potassium hydroxide in tert-butyl alcohol. J. Org. Chem. 41, 3769-3770.
64. Sawaki, Y., and Ogata, Y. (1981) Mechanism of the reaction of nitriles with alkaline hydrogen peroxide. Reactivity of peroxycarboximidic acid and application to superoxide ion reaction. Bull. Chem. Soc. Jpn. 54, 793-799.
65. Katritzky, A. R., Pilarski, B., and Urogdi, L. (1989) Efficient conversion of nitriles to amides with basic hydrogen peroxide in dimethyl sulfoxide. Synthesis 949-950.
66. (a) Bach, R. D., and Knight, J. W. (1979) Elimination reactions in dimethyl sulfoxide solution. The effective base with potassium tert-butoxide. Tetrahedron Lett. 40, 3815-3818.
67. (b) Exner, J. H., and Steiner, E. C. (1974) Solvation and ion pairing of alkali-metal alkoxides in dimethyl sulfoxide. Conductometric studies. J. Am. Chem. Soc. 96, 1782-1787.
68. (c) Bartsch, R. A. (1975) Ionic association in base-promoted beta-elimination reactions. Acc. Chem. Res. 8, 239-245.
69. Bunch, A. W. (1998) Biotransformation of nitriles by rhodococci. Antonie van Leeuwenhoek 74, 89-97.
70. (a) Crosby, J., Moilliet, J., Parratt, J. S., and Turner, N. J. (1994) Regioselective hydrolysis of aromatic dinitriles using a whole cell catalyst. J. Chem. Soc., Perkin Trans. 1, 1679-1687.
71. (b) Kakeya, H., Sakai, N., Sugai, T., and Ohta, H. (1991) Microbial hydrolysis as a potent method for the preparation of optically active nitriles, amides and carboxylic acids. Tetrahedron Lett. 32, 1343-1346.
72. Huang, W., Jia, J., Cummings, J., Nelson, M., Schneider, G., and Lidqvist, Y. (1997) Crystal structure of nitrile hydratase reveals a novel iron centre in a novel fold. Structure 5, 691-699.
73. Nagashima, S., Nakasako, M., Dohmae, N., Tsujimura, M., Takio, K., Odaka, M., Yohda, M., Kamiya, N., and Endo, I. (1998) Novel non-heme iron center of nitrile hydratase with a claw setting of oxygen atoms. Nat. Struct. Biol. 5, 347-351.